Age 8 and up
Swim Requirement Must supply proof of ability to swim 75 feet and tread water for 90 seconds. Download our Proof of Swimming Ability Form here.
Experience Requiment No experience necessary. New sailors welcome.
Limits One session per child per summer. Each session is 4 - 5 days long, depending on the week.
Daily Schedule

9:30 AM - 3:30 PM*

*drop off begins at 9:15 AM; extended day option available (see FAQ)

2016 Dates


  • Tues 7/5 - Fri 7/8
  • Mon 7/11 - Fri 7/15
  • Mon 7/18 - Fri 7/22
  • Tues 8/16 - Fri 8/19


Jamaica Pond* (Boston residents only - proof of residency required!):

  • Tue 7/5 - Fri 7/8
  • Mon 7/11 - Fri 7/15
  • Mon 7/18 - Fri 7/22
  • Tue 7/26 - Fri 7/29
  • Mon 8/1 - Fri 8/5
  • Mon 8/8- Fri 8/12

* Jamaica Pond dates are tentative and subject to change.

**There is the potential for another Step 1 class at UMASS Boston from 8/16 - 8/19.  If interested, please indicate on the lottery registration form.  

Locations Charlestown and Jamaica Pond
Cost $210 for 4 day program and $250 for 5 day program (fee is based on a sliding scale)

Course Description

Step 1 is our "Sailing 101" course, offered to children ages 8-and-up from throughout the Greater Boston Area. Each student attends Step 1 for one four-five day session. During this time they are introduced to the basics of sailing theory and are exposed to boating on Boston Harbor. Students are taught through a fun, high-energy, game-based approach, learning aboard stable keelboats, Rhodes-19s. No prior sailing experience necessary, though all students must be able to demonstrate a minimum level of swimming competency. Please refer to the registration FAQ section for more details. At Jamaica Pond, students will use a combination of small sailboats.


Sunday, 01 February 2009 21:23

Commitment to Safety

Written by

Commitment to Safety

At Courageous we place tremendous importance on safety. We are constantly taking measures to impress upon our students that a safe sailor is a good sailor. Below is a partial listing of our safety regulations, rigorous guidelines that have given Courageous one of the best safety records on Boston Harbor.

  1. Life jackets must be worn at all times while on the dock. No student is allowed throug the dock gate without a life jacket.
  2. Most of our instructors are US Sailing Instructor Certified and all have attended Courageous training programs.
  3. A head instructor is always on duty to supervise operations.
  4. A safety launch accompanies all classes with at least one launch on stand-by at the Courageous pier.
  5. Our student-to-instructor ratio is 3:1 — one of the best in the industry.
  6. All launches are equipped with VHF radios for fast communication with each other, the boathouse, and if necessary the Boston Harbor Police and US Coast Guard.
  7. Courageous has a conservative foul weather policy. Boats are recalled or kept at the dock in bad weather and forecasts are monitored constantly.
  8. All students in the program must be able to swim at least 25 yards and tread water for 90 seconds.



Several competitive high school sailing teams train at Courageous' sites in Charlestown or Jamaica Pond. Whether a school is putting together a team for the very first time or has an already established team that needs a new place to sail, Courageous has been able to come through for local schools.


Current high schools that train with Courageous include BB&N, Boston Latin, The British School of Boston, Codman Academy Charter Public School, and Boston Public Schools (district-wide team). To find out if your high school can participate, email or call Kate Henderson at (617) 242-3821 ext. 12.


Boston Public Schools' District-Wide Sailing Team
Thanks to an outpouring of community support, in March of 2011, the BPS district-wide sailing team took the water for the first time with a small, but extremely dedicated crew of sailors. The team was comprised of students from all parts of Boston. They had one thing in common: a passion for sailing. The season culminated in a strong C-Division finish at the Mass Bay League Championship. The team’s success was highlighted in numerous news articles, and we were honored that it received national praise in the Council for Great City Schools’ June/July 2011 issue of Urban Educator.

Now entering their second season, returning team members, under the tutelage of veteran Courageous coach Chris DuBois, will return to lead a larger Varsity program and set the stage for a new JV team.



BPS Students: Interested in Sailing for Boston Public?

**Note: If you attend Boston Latin School, this isn't for you -- you already have a team. Contact Dave and Cha -- they're your BLS sailing coaches!

  • Requirements:
    • No sailing experience necessary!
    • Must be able to swim the length of a pool, unassisted, any stroke, and tread water for 90 seconds.
    • Must be able to commute to Charlestown Navy Yard in time for 3:45 (practice start time) and provide own transportaiton home.
  • Sailing Season Dates: March 26 - June 3, 2012 (tentative)
  • Practice Times: Monday, Wednesday, Friday, 3:30 pm - 6:30 pm
  • Practice Location: Courageous Sailing, Charlestown Navy Yard (directions)
  • Waiver Forms: Download here. Must be signed by parent/legal guardian in order to participate.
  • Medical Forms: Download here. Must be completed and signed by a parent/legal guardian in order to participate.
CYRT 2008

Courageous Keelboat Kickoff Regatta, 3/31 - Registration Deadline: Monday, 3/26

First Event of Mass Bay League B Division Fleet Race Series

Please join us for the 4th Courageous Keelboat Kickoff Regatta. The event is a great opportunity to get a lot of kids on the water, early in the season.

Please note:

  • Skippers must be able to sail a Rhodes 19keelboat comfortably and safely in tight quarters, onto and off of a fixed dock.
  • Each "slot" represents 6 sailors (3 in A div, 3 in B). At full capacity (20+ Rhodes 19s) we can accomodate 120+ sailors.
  • This event is open to all MBL and NESSA teams, with 2 slots reserved for each MBL B-Div team.  Registrations will be taken in the order they are received.  All schools may register a second or third team, but these will be waitlisted until the registration deadline, Monday, 3/26. 

The NOR is below.  Let me know if you have any questions, and please register early.

Dave DiLorenzo
Boston Latin School Head Coach

Notice of Race

2012 Courageous Keelboat Kickoff Regatta (First Event of Mass Bay League B Division Fleet Race Series)

Date: Saturday, March 31, 2012
Location: Courageous Sailing Center, Boston Harbor

Report Time: 0900
Boats: Rhodes 19 Keelboats (3 person crews)
Format: A and B Division
Rules: RRS, ISSA PR, NESSA PR and By-laws, including Article L
Registration Deadline: Monday, March 26, 2012 at 1700 hours

Registration: To register, send an email to Cha OConnell that includes the following information:

1. Name of school
2. Contact info for the coach (phone, email)
3. Number of slots.  (Schools may request any number of slots. MBL B division teams requesting more than 2 slots, and all other teams requesting more than 1 slot, will be kept on the waitlist until after the registration deadline, at which time they will be added in the order they were received, one per school, until all slots have been filled.)
4. In subject line please put "Courageous KeelboatKickoff/School Name"

Waiver Forms:
Team members and coaches must complete the following waiver forms and submit at check-in on raceday. Please download and complete in advance to save time:
Courageous Youth Program, (c) Russ Bolt 2008


We teach students to embody the values of our COURAGE curriculum, both on the water and off. As they learn to sail, participate in team-building activities and discussions, and engage in community service projects around the harbor, our students cultivate essential life skills including those in communication, teamwork and leadership.

What is Courage?

Courage is the quality of spirit that enables you to face difficulties with self-possession, confidence and resolution. COURAGE also represents a set of values which empowers people to become leaders in school, communities, and the workplace.




  • Definition: Works with others towards common goals.
  • Recipie: Communication • Compromise • Patience
  • Lingo: We can do this together. How can I help? We are a team.
  • Actions: Actively participates. Encourages others. Communicates effectively.




  • Definition: Listen's to others ideas; is willing to consider new ideas.
  • Recipie:Tolerance •Friendliness • Sportsmanship
  • Lingo: What do you think? I never thought of it that way. That's a good idea.
  • Actions: Considers others' input. Welcomes change.




  • Definition: Accepts others with tolerance and sympathy.
  • Recipie:Forgiveness • Communication • Sympathy • Good Listening Skills
  • Lingo: I see what you mean. It's okay to make mistakes.Let's try again.
  • Actions: Sees a situation from someone else's point of view.




  • Definition: Chooses between right and wrong; keeps their word.
  • Recipie:Accountability •Punctuality • Follow-Through • Trustworthy
  • Lingo: I will. You can count on me. That was my fault.
  • Actions: Arrives to class on-time. Brings all equipment on boat. Keeps boat clean.



  • Definition: Seeks out new experiences with enthusiasm.
  • Recipie:Effort •Participation •Dedication • Interest
  • Lingo: I'm willing to try.This is fun. Can I do that?
  • Actions: Tries something unfamiliar. Overcomes fear.




  • Definition: Looks for ways to positively contribute to their community and the environment.
  • Recipie:Passion •Hard Work•Stewardship • Generosity
  • Lingo: I want to do more.How can I help?
  • Actions: Picks up trash on the pier. Lends a hand when needed.




  • Definition: Undertakes projects with imagination and initiative.
  • Recipie:Motivation • Creativity • Imagination •Learning •Knowledge
  • Lingo: How does this work? I know I can do it. Let's try this.
  • Actions: Does not give up. Tries new approaches to problems.


photo (c) Russ Bolt 2008


The Courageous Youth Program does so much more than just teach sailing.  At Courageous, we aim to transform kids' lives through the sport of sailing.  Our instruction team works to foster a love of sailing, adventure and the outdoors.  They give students the values, skills and confidence that they will need to thrive in their communities and their lives.

Leadership Training

We teach students to empldy the values of our COURAGE curriculum, both on the water and off.  As they learn to sail, participate in team-building activities and discussions, and engage in community service projects around the harbor, our students cultivate essential life skills including those in communication, teamwork and leadership.

Environmental Education

Courageous collaborates with Save the Harbor/Save the Bay and Sailor's for the Sea to teach our students an active respect for the waters on which they sail and the surrounding ecosystem,  Students learn about the many organisms and natural resources of Boston Harbor and, under the guidance of our instruction team, initiate beach clean-ups, water quality testing, and other activities to help protect some of our city's most precious environmental treasures.

Professional Development/Job Training
Our youth students often advance to become Courageous employees, gaining valuable experience that gives them a jump start on entering the working world. Through our innovative Instructor-in-Training (IIT) and Continuing Education programs, staff members hone not only their sailing and boat maintenance skills, but also their skills in teaching, leadership and professionalism. [more...]

Adaptive Sailing

Courageous is the largest organization of its kind in the Boston area to offer free sailing programs and activities to people with autism, developmental disabilities, blindness, and diabetes. These programs have produced regional, national and even world champions!  With Courageous, members of these populations (mostly youth and young adults), who regularly find themselves barred from sailing and similar activities, gain a variety of physical, social, and psychological benefits, many of which are unique to the experience of sailing itself. While sailing in majestic Boston Harbor, participants build skills in teamwork, physical coordination, self-reliance, abstract thought, and leadership as well as technical knowledge of a dynamic sport. These elements rarely coincide in other activities open to these groups.
At Courageous, the goal is not only to improve our existing opportunities for these groups, but to expand them as well. Courageous provides the special know-how, equipment, support, and understanding, while working to expand the breadth and depth of personnel training in these areas. In doing so, Courageous can continue to provide more and more people with blindness, diabetes, autism and other developmental disabilities with the opportunity to experience the unique joy and exhilaration of sailing.
Beyond offering the simple pleasures of the sport, the goals of Courageous Enabled Sailing programs are that our participants gain: (A) knowledge of sailing, the environment and leadership. (B) Intrapersonal strength, including self-confidence, self-esteem, well being and sense of adventure. For blind and developmentally disabled youth, taking the helm of a sailboat and navigating it is an incredibly empowering experience, one that instills pride, self-confidence, and a sense of capability. (C) Interpersonal skills, including teamwork, communications, conflict resolution, and sense of belonging. The experience of sailing with a crew and executing maneuvers as part of a team counteracts the feelings of isolation and loneliness that blind, developmentally disabled and autistic children are often subject to. (D) Close contact with and commitment to the natural environment of Boston Harbor. (E) Improved motor and coordination skills that the sport of sailing requires. (F) The calmness and confidence that sailing in such a beautiful locale instills in all those who do it, but that is most especially beneficial to autistic and other developmentally impaired individuals. The skills gained through our collaborative programs will remain with them long after they have stepped off the boat and become more closely connected to their families, classrooms, jobs, and communities.
The programs at Courageous primarily serve youth and young adults with disabilities ranging from intellectual and developmental disabilities such as autism to blindness and insulin-dependent diabetes. We reach these populations through our partnerships with The Barton Center for Diabetes Education and their Summer Adventure Programs, Special Olympics of Massachusetts, The Carroll Center for the Blind and the Heart of Sailing Foundation.
Tuesday, 20 January 2009 17:27

Quotes 7

Written by
“We were absolutely thrilled with the sailing program! The staff were exceptional! They were so enthusiastic about sailing that their attitude was contagious!”